Hydrochloric Acid → (7-Methoxy-1-naphthyl)(oxo)acetic acid

HRID 1099495

Reaction equation

HRID 1099495 reaction equation
C1OCCOCCOCCOCCOCC[O:3]C1.[CH3:19][O:20][C:21]1[CH:31]=[CH:30][C:29]2[C:32]3[C:22]=1[C:23](=[O:34])[C:24](=[O:33])[C:25]=3[CH:26]=[CH:27][CH:28]=2.O.Cl>CS(C)=O>[CH3:19][O:20][C:21]1[CH:22]=[C:32]2[C:29]([CH:28]=[CH:27][CH:26]=[C:25]2[C:24](=[O:33])[C:23]([OH:34])=[O:3])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2855718-Crown-6HCID 22502643-Methoxyacenaphthoquinone

Product 1

HCID 14462720(7-Methoxy-1-naphthyl)(oxo)acetic acidYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a reactor, 4 mg of 18-crown-6 ether and then 230 mg of NaNH2 are successively introduced into a suspension of 100 mg of 3-methoxyacenaphthoquinone in 1 ml of DMSO. The mixture is stirred for 30 minutes at ambient temperature. Water (2 ml) is then added, followed by 2N HCl solution (3 ml). After two extractions with ethyl acetate, the solvents are dried over Na2SO4 and then evaporated off to yield the title product in the form of a yellow solid in a yield of 88% and with a chemical purity of more than 94%.

Workup

  1. extractionAfter two extractions with ethyl acetate
  2. dry with materialthe solvents are dried over Na2SO4
  3. customevaporated off

Sources & evidence

ORD record
ord-4a1196c80d5a47079f125b06fd9b6367
Source dataset
uspto-grants-2012_03
Patent number
US08143449B2

Linked notes

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